One-pot synthesis of 4,8-dialkylbenzo[1,2-b:4,5-b']dithiophenes

Ted M. Pappenfus, Daniel T. Seidenkranz, Eric W. Reinheimer

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    Abstract

    Two-step, one-pot syntheses are described for the preparation of 4,8-dialkylbenzo[1,2-b:4,5-b']dithiophenes (BDTs) from alkyllithium or alkyl Grignard reagents. The yields for various alkyl groups used in this procedure are comparable with or exceed those of previously reported methods. The electronic and redox properties of dialkyl-BDTs are compared with the dialkoxy-BDT, 4,8-bis(hexyloxy)benzo[1,2-b:4,5-b']dithiophene. The stabilized HOMO levels of dialkyl-BDTs suggest they are promising building blocks for use in organic photovoltaics such as bulk heterojunction solar cells.

    Original languageEnglish (US)
    Pages (from-to)355-364
    Number of pages10
    JournalHeterocycles
    Volume85
    Issue number2
    DOIs
    StatePublished - Jan 30 2012

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    Pappenfus, T. M., Seidenkranz, D. T., & Reinheimer, E. W. (2012). One-pot synthesis of 4,8-dialkylbenzo[1,2-b:4,5-b']dithiophenes. Heterocycles, 85(2), 355-364. https://doi.org/10.3987/COM-11-12390